174174-99-3Relevant articles and documents
Synthesis of 5'-fluoro-5'-deoxy- and 5'-amino-5'-deoxytoyocamycin and sangivamycin and some related derivatives
Sharma,Li,Ledvina,Bobek
, p. 1831 - 1852 (2007/10/02)
A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azido-5-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.